Literature DB >> 31407847

Bio-inspired Total Synthesis of Twelve Securinega Alkaloids: Structural Reassignments of (+)-Virosine B and (-)-Episecurinol A.

Kevin Antien1, Aitor Lacambra1,2, Fernando P Cossío2, Stéphane Massip3, Denis Deffieux1, Laurent Pouységu1, Philippe A Peixoto1, Stéphane Quideau1.   

Abstract

The so-called Securinega alkaloids constitute a class of tetracyclic biologically active specialised metabolites isolated principally from subtropical plants belonging to the Phyllanthaceae family. Following a strategy based on alternative hypotheses for their biosynthesis, an easy and time-efficient divergent synthesis enabled access to twelve of those alkaloids featuring (neo)(nor)securinane skeletons. Moreover, this work permitted to reassign the absolute configurations of (+)-virosine B and (-)-episecurinol A.
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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Keywords:  aldol reaction; alkaloids; biomimetic synthesis; natural products; total synthesis

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Year:  2019        PMID: 31407847     DOI: 10.1002/chem.201903122

Source DB:  PubMed          Journal:  Chemistry        ISSN: 0947-6539            Impact factor:   5.236


  1 in total

1.  Collective total synthesis of C4-oxygenated securinine-type alkaloids via stereocontrolled diversifications on the piperidine core.

Authors:  Sangbin Park; Gyumin Kang; Chansu Kim; Dongwook Kim; Sunkyu Han
Journal:  Nat Commun       Date:  2022-09-02       Impact factor: 17.694

  1 in total

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